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Cycloanchinopeptolide C

Family: Animalia - Hymedesmiidae
Kingdom: Animalia
Class: Alkaloid
- Subclass: Peptide Alkaloid

Canonical Smiles	NC(=N)NCC[C@H]1[C@@]2(O)C(=O)NCC(=O)N[C@@H]3[C@H](NC(=O)CN[C@H]2C(=O)[C@]1(O)CCCNC(=N)N)[C@H]([C@H]3c1ccc(cc1)O)c1ccc(cc1)O
InChI	InChI=1S/C33H44N10O8/c34-30(35)38-12-1-11-32(50)20(10-13-39-31(36)37)33(51)27(28(32)48)40-14-21(46)42-25-23(16-2-6-18(44)7-3-16)24(17-4-8-19(45)9-5-17)26(25)43-22(47)15-41-29(33)49/h2-9,20,23-27,40,44-45,50-51H,1,10-15H2,(H,41,49)(H,42,46)(H,43,47)(H4,34,35,38)(H4,36,37,39)/t20-,23+,24-,25-,26+,27+,32+,33+/m1/s1
InChIKey	QFZWTRIATPJVAF-ROVJCKOLSA-N
Formula	C₃₃H₄₄N₁₀O₈
HBA	11
HBD	14
MW	708.78
Rotatable Bonds	9
TPSA	321.12
LogP	-3.17
Number Rings	5
Number Aromatic Rings	2
Heavy Atom Count	51
Formal Charge	0
Fraction CSP3	0.45
Exact Mass	708.33
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Anchinoe tenacior	Hymedesmiidae	Animalia	252958

Showing of synonyms

Casapullo A, Minale L, et al. (1994). Four new dimeric peptide alkaloids, anchinopeptolides B-D, and cycloanchinopeptolide C, congeners of anchinopeptolide A, from the mediterranean marine sponge Anchinoe tenacior. Journal of Natural Products,1994,57(9),1227-1233. [View] [PubMed]

Pubchem: 162817184

Nmrshiftdb2: 60045921

No compound-protein relationship available.

SMILES: c1ccccc1C2C(c3ccccc3)C(C24)NC(=O)CNC(=O)C5C(C(=O)CC5)NCC(=O)N4

Level: 2

Mol. Weight: 708.78 g/mol

SMILES: c1ccccc1C2CC(C23)NC(=O)CNC4C(CCC4=O)C(=O)NCC(=O)N3

Level: 1

Mol. Weight: 708.78 g/mol

SMILES: c1ccccc1C2CC(C23)NC(=O)CNC(=O)C4C(C(=O)CC4)NCC(=O)N3

Level: 1

Mol. Weight: 708.78 g/mol

SMILES: C1CC(C12)NC(=O)CNC(=O)C3C(C(=O)CC3)NCC(=O)N2

Level: 0

Mol. Weight: 708.78 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 708.78 g/mol

Binding assays against the following receptors

Human b2 bradykinin and neuropeptide gamma receptors

Somatostatin

Absorption

Caco-2 (logPapp): -6.14
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.060
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 277.12

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.500
Plasma Protein Binding: 69.83
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 2.120
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -6.120
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.760
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 8.300
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -490532.010
Rat (Acute): 2.610
Rat (Chronic Oral): 1.620
Fathead Minnow: 627.130
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 45287.210
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -1.410
Log(P): -2.29
Log S: -0.31
Log(Vapor Pressure): -1494.38
Melting Point: 268.19
pKa Acid: 3.42
pKa Basic: 9.54

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9366
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9366
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.9218
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.9218
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.9158
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.9158
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.9021
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.9021
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8884
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8884
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8552
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8552
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.8433
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.8433
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8344
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8344
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8335
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8335
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8313
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8313
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8273
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8273
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7939
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7939
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.7917
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.7917
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7913
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7913
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7809
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7809
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.7766
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.7766
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7740
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7740
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7679
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7679
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7671
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7671
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7606
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7606
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7605
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7605
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7597
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7597
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7535
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7535
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7508
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7508
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7503
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7503
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7499
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7499
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7485
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7485
Catalase-peroxidase 2	O59651	KATG2_HALMA	Haloarcula marismortui	2	0.7409
Catalase-peroxidase 2	O59651	KATG2_HALMA	Haloarcula marismortui	2	0.7409
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7404
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7404
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7392
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7392
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7375
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7375
Orotidine 5'-phosphate decarboxylase	Q5L0U0	PYRF_GEOKA	Geobacillus kaustophilus	3	0.7326
Orotidine 5'-phosphate decarboxylase	Q5L0U0	PYRF_GEOKA	Geobacillus kaustophilus	3	0.7326
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7323
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7323
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7302
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7302
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7297
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7297
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7291
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7291
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7286
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7286
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7260
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7260
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7202
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7202
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7197
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7197
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	3	0.7185
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	3	0.7185
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7172
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7172
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7161
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7161
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7153
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7153
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7151
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7151
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7146
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7146
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7109
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7109
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7107
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7107
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7094
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7094
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7093
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7093
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7082
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7082
Dihydrofolate reductase	P00381	DYR_LACCA	Lacticaseibacillus casei	3	0.7079
Dihydrofolate reductase	P00381	DYR_LACCA	Lacticaseibacillus casei	3	0.7079
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7044
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7044
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7042
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7042
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7041
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7041
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	2	0.7038
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	2	0.7038
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7027
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7027
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7019
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7019

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